Hydrochloric Acid → HCID 178442452, compound

HRID 216400Notes

Reaction equation

Cl.[CH3:2][C:3]([CH3:48])([CH2:46][CH3:47])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=3)=[CH:35][CH:34]=2)[NH:31][CH3:32])[N:8](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1>CO>[CH3:2][C:3]([CH3:48])([CH2:46][CH3:47])[CH2:4][C:5]1[N:6]=[C:7]([CH2:29][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=3)=[CH:35][CH:34]=2)[NH:31][CH3:32])[NH:8][CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Hydrogen chloride (4 M in dioxane) (2.6 mL, 10.5 mmol) was added to a solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine (1.3 g, 2.1 mmol) in methanol (20 mL). After stirring at 60° C. for 1 h, volatiles were removed. The residue was partitioned between 1 N hydrochloric acid and hexane/diethyl:ether (3:1). The aqueous phase was washed with hexane/diethyl ether (3:1), basified with saturated aqueous sodium carbonate and extracted with ethyl acetate. Combined extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound. Purification by HPLC (Gilson; Chiralcel AD column; 50% isopropanol/heptane) afforded the pure enantiomers. (M+H) found 381.

Workup

customvolatiles were removed
customThe residue was partitioned between 1 N hydrochloric acid and hexane/diethyl
washThe aqueous phase was washed with hexane/diethyl ether (3:1)
extractionextracted with ethyl acetate
dry with materialCombined extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ed85cb33f3004c8480bc88dce123698d
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193228B2

Reaction notes

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